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Chemistry of Heterocyclic Compounds

, Volume 55, Issue 4–5, pp 392–396 | Cite as

Acetic aldehyde in multicomponent synthesis of azolopyrimidine derivatives in water

  • Irina G. Tkachenko
  • Sergey A. KomykhovEmail author
  • Eugene S. Gladkov
  • Vladimir I. Musatov
  • Valentyn A. Chebanov
  • Sergey M. Desenko
Article

Three-component reaction of 3-amino-1H-1,2,4-triazole or 5-amino-2H-1,2,3-triazole derivatives, acetaldehyde, and 1,3-dicarbonyl compounds (acetylacetone or β-keto esters) in water under microwave irradiation leads to regioselective formation of 4,7-dihydro[1,2,4]-triazolo- and 4,7-dihydro[1,2,3]triazolo[1,5-a]pyrimidines. Using ethyl 4,4,4-trifluoro-3-oxobutanoate as 1,3-dicarbonyl compound under the same conditions allows to obtain the corresponding 5-hydroxy-4,5,6,7-tetrahydro derivatives, which fail to dehydrate in the reaction medium.

Keywords

acetaldehyde 1,3-dicarbonyl compound 1,2,3-triazole 1,2,4-triazole triazolo[1,5-a]pyrimidine microwave-assisted synthesis multicomponent reaction 

Notes

Authors thank National Academy of Sciences of Ukraine for financial support in the frame of projects ''Creation of modern basis for obtaining and analyzing substances and components of materials for pharmaceutical purposes'' (0119U100727) and ''Investigation of structural features of nitrogen-containing heterocycles with potential biological activity'' (0119U100716).

Supplementary material

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ESM 1 (PDF 485 kb)

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Irina G. Tkachenko
    • 1
    • 2
    • 3
  • Sergey A. Komykhov
    • 1
    • 2
    Email author
  • Eugene S. Gladkov
    • 1
    • 2
  • Vladimir I. Musatov
    • 1
  • Valentyn A. Chebanov
    • 1
    • 2
  • Sergey M. Desenko
    • 1
    • 2
  1. 1.State Scientific Institution “Institute for Single Crystals”National Academy of Sciences of UkraineKharkivUkraine
  2. 2.V. N. Karazin Kharkiv National UniversityKharkivUkraine
  3. 3.Kharkiv Forensic Science CenterMinistry of Internal Affairs of UkraineKharkivUkraine

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